Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H24O |
Molecular Weight | 220.3505 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C
InChI
InChIKey=NLZUEZXRPGMBCV-UHFFFAOYSA-N
InChI=1S/C15H24O/c1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h8-9,16H,1-7H3
Molecular Formula | C15H24O |
Molecular Weight | 220.3505 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Butylated hydroxytoluene, commonly known as BHT, is an organic compound that is used in the food, cosmetic, and pharmaceutical industry as an antioxidant. BHT is a substituted derivative of phenol. BHT helps to prevent the formation of free radicals and oxidation. When used in food products, it delays oxidative rancidity of fats and oils, and prevents loss of activity of oil-soluble vitamins. It may be found in pharmaceutical gels, creams and liquid or gelatin capsules, tablets and other pharmaceutical dosage forms. The ability of oral BHT to lead to cancer is a controversial topic, but most food industries have replaced it with butylated hydroxyanisole (BHA). BHT was first used as an antioxidant food additive in 1954. BHT does have other commercial uses, as in animal feeds and in the manufacture of synthetic rubber and plastics, where it also acts as an antioxidant. The U.S. Food and Drug Administration has deemed that BHT is safe enough when used in limited concentrations. It currently permits its use in concentrations of about 0.01% to 0.02% in most foods. As an emulsion stabilizer in shortening, it may be used in a somewhat higher concentration, 200 parts per million.
CNS Activity
Sources: http://naturaldatabase.therapeuticresearch.com/nd/PrintVersion.aspx?id=1071&AspxAutoDetectCookieSupport=1
Curator's Comment: It may cross the blood brain barrier, causing psychotropic symptoms
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19231207 |
630.0 nM [Ki] | ||
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Inactive ingredient | A-TEAM Approved UseUSE HELPS PROTECT AGAINST SUNBURN Launch Date2014 |
PubMed
Title | Date | PubMed |
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Inhibition by butylated hydroxytoluene and its oxidative metabolites of DMBA-induced mammary tumorigenesis and of mammary DMBA-DNA adduct formation in vivo in the female rat. | 1992 Jun |
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MAP: microwave-assisted extraction of fatty acids and Py/GC/MS analysis of selected insects. | 2001 |
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Estrogenic activity of phenolic additives determined by an in vitro yeast bioassay. | 2001 Feb |
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Heteropteris aphrodisiaca O. Machado : effects of extract BST 0298 on the oxidative stress of young and old rat brains. | 2001 Nov |
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[Determination of 2,6-di-tertbutyl-4-methylphenol in an aviation jet fuel by high performance liquid chromatography]. | 2002 Jul |
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Hydrogen bonding between phenols and fatty acid esters: (1)H NMR study and ab initio calculations. | 2002 Jul 11 |
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A lipoxygenase inhibitor from Aspergillus niger. | 2002 Mar |
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Analysis of the antioxidant butylated hydroxytoluene (BHT) in water by means of solid phase extraction combined with GC/MS. | 2002 May |
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The uptake of tocopherols by RAW 264.7 macrophages. | 2002 Oct 15 |
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Contact allergy to the monomers in p-tert-butylphenol-formaldehyde resin. | 2002 Sep |
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Characterization of specifically oxidized apolipoproteins in mildly oxidized high density lipoprotein. | 2003 Feb |
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Sequestering ability of butylated hydroxytoluene, propyl gallate, resveratrol, and vitamins C and E against ABTS, DPPH, and hydroxyl free radicals in chemical and biological systems. | 2003 Feb 12 |
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Control of Clostridium perfringens germination and outgrowth by buffered sodium citrate during chilling of roast beef and injected pork. | 2003 Mar |
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A critical evaluation of the factors determining the effect of intramolecular hydrogen bonding on the O-H bond dissociation enthalpy of catechol and of flavonoid antioxidants. | 2004 Feb 20 |
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Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites. | 2004 Jul |
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Inactivation of endoplasmic reticulum bound Ca2+-independent phospholipase A2 in renal cells during oxidative stress. | 2004 Jun |
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[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations]. | 2004 May |
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Relative antioxidant capacities of propofol and its main metabolites. | 2004 Nov |
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Chemical constituents of Morinda citrifolia fruits inhibit copper-induced low-density lipoprotein oxidation. | 2004 Sep 22 |
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New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents. | 2006 Aug 15 |
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Enhancement of tumor invasion depends on transdifferentiation of skin fibroblasts mediated by reactive oxygen species. | 2006 Jul 1 |
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Synthesis and antioxidant activity of [60]fullerene-BHT conjugates. | 2006 Jun 2 |
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Cytokine response to lipoprotein lipid loading in human monocyte-derived macrophages. | 2006 Jun 26 |
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Evaluation of the antioxidant capacity of limonin, nomilin, and limonin glucoside. | 2006 May 31 |
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Lipophilic hydroxytyrosyl esters. Antioxidant activity in lipid matrices and biological systems. | 2006 May 31 |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Does immune stimulation or antioxidant therapy reduce MNU-induced placental damage via activation of Jak-STAT and NFkappaB signaling pathways? | 2007 May-Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2988845
The effect of topical therapy with 15% Butylated hydroxytoluene in mineral oil on the course of recurrent herpes simplex labialis was examined in 30 patients in a double-blind, placebo-controlled pilot study.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1900157
Curator's Comment: The effect of Butylated hydroxytoluene on the oxidation of low density lipoproteins in relation to prostacyclin synthesis was investigated in the prescence of rabbit smooth muscle cells (SMC) and Fe-containing culture medium.
Butylated hydroxytoluene (BHT) inhibited lipoprotein oxidation by IC50 values of 0.8 uM
Substance Class |
Chemical
Created
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Record UNII |
1P9D0Z171K
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
22105
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JECFA EVALUATION |
INS-321
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CODEX ALIMENTARIUS (GSFA) |
INS-321
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NCI_THESAURUS |
C275
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CFR |
21 CFR 172.115
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34247
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m2820
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100000076384
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CHEMBL146
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6347
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1082708
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C322
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1P9D0Z171K
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1P9D0Z171K
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128-37-0
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204-881-4
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DTXSID2020216
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BUTYLATED HYDROXYTOLUENE
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1848
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1147
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31404
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BUTYLATED HYDROXYTOLUENE
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PRIMARY | Description: Colourless crystals or a white or almost white, crystalline powder; odour, faint and characteristic. Solubility: Practically insoluble in water; freely soluble in ethanol (~750 g/l) TS, acetone R, ether R, and arachis oil R. Category: Antioxidant. Storage: Butylated hydroxytoluene should be kept in a well-closed container, protected from light. |
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ACTIVE MOIETY |
http://apps.who.int/phint/pdf/b/Jb.6.1.65.pdf
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